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An unusual adjective that refers to both the subject and the author simultaneously.

Of the subject: Having the most wins.

Of the author: Being an idiot who can't be bothered to look up a real word.
"Michael Phelps is the winningest athlete in Olympic history"
by Tom2003 August 20, 2008
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Apr 22 Word of the Day
When you eat dirt for the first time and leave your family to build a shack in the woods
Bro since I got dirtpilled on Tuesday I have made sooo many worm friends and made them soo many little houses to get married in. Me? Lonely? No you’re the lonely one u lawn owning freak
via giphy
by ecogoth December 30, 2020
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2
This is not a word, though used by some people. As well as explained to be a word Winningest is not a word.
Announcer: That coach is the winningest coach in hockey currently.
Me: Dude, that's not a word.
by Spelling Nazi misspellings die December 31, 2010
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4
to have either the most wins, or the highest win percentage, depending on the sportscaster
Joe Pa will never be this winningest coach no matter how long he's in the game
by BMG December 17, 2002
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